WO1991003944A1 - Triglycerides a teneur en calories reduite dans des aliments - Google Patents

Triglycerides a teneur en calories reduite dans des aliments Download PDF

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Publication number
WO1991003944A1
WO1991003944A1 PCT/US1990/005306 US9005306W WO9103944A1 WO 1991003944 A1 WO1991003944 A1 WO 1991003944A1 US 9005306 W US9005306 W US 9005306W WO 9103944 A1 WO9103944 A1 WO 9103944A1
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WIPO (PCT)
Prior art keywords
composition according
carbons
fatty acid
fat
group
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Application number
PCT/US1990/005306
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English (en)
Inventor
Peter S. Givens, Jr.
Edward L. Wheeler
Ronald P. D'amelia
Michael S. Otterburn
Gilbert A. Leveille
John W. Finley
Lawrence P. Klemann
Original Assignee
Nabisco Brands, Inc.
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Publication of WO1991003944A1 publication Critical patent/WO1991003944A1/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G1/00—Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
    • A23G1/30—Cocoa products, e.g. chocolate; Substitutes therefor
    • A23G1/32—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds
    • A23G1/36—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds characterised by the fats used
    • A—HUMAN NECESSITIES
    • A21—BAKING; EDIBLE DOUGHS
    • A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
    • A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
    • A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
    • A21D2/14—Organic oxygen compounds
    • A21D2/16—Fatty acid esters
    • A21D2/165—Triglycerides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C11/00—Milk substitutes, e.g. coffee whitener compositions
    • A23C11/02—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins
    • A23C11/04—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins containing non-milk fats but no non-milk proteins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C19/00—Cheese; Cheese preparations; Making thereof
    • A23C19/02—Making cheese curd
    • A23C19/055—Addition of non-milk fats or non-milk proteins, polyol fatty acid polyesters or mineral oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/001—Spread compositions
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/003—Compositions other than spreads
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/015—Reducing calorie content; Reducing fat content, e.g. "halvarines"
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G1/00—Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
    • A23G1/30—Cocoa products, e.g. chocolate; Substitutes therefor
    • A23G1/32—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds
    • A23G1/36—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds characterised by the fats used
    • A23G1/38—Cocoa butter substitutes
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G1/00—Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
    • A23G1/30—Cocoa products, e.g. chocolate; Substitutes therefor
    • A23G1/56—Cocoa products, e.g. chocolate; Substitutes therefor making liquid products, e.g. for making chocolate milk drinks and the products for their preparation, pastes for spreading, milk crumb
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/343—Products for covering, coating, finishing, decorating
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/346—Finished or semi-finished products in the form of powders, paste or liquids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G9/00—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor
    • A23G9/32—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by the composition containing organic or inorganic compounds
    • A23G9/327—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by the composition containing organic or inorganic compounds characterised by the fatty product used, e.g. fat, fatty acid, fatty alcohol, their esters, lecithin, glycerides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G9/00—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor
    • A23G9/52—Liquid products; Solid products in the form of powders, flakes or granules for making liquid products ; Finished or semi-finished solid products, frozen granules
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/40—Feeding-stuffs specially adapted for particular animals for carnivorous animals, e.g. cats or dogs
    • A23K50/42—Dry feed
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L9/00—Puddings; Cream substitutes; Preparation or treatment thereof
    • A23L9/20—Cream substitutes
    • A23L9/22—Cream substitutes containing non-milk fats but no proteins other than milk proteins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/30—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with trihydroxylic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C11C3/10—Ester interchange
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G2200/00—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents
    • A23G2200/08—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents containing cocoa fat if specifically mentioned or containing products of cocoa fat or containing other fats, e.g. fatty acid, fatty alcohol, their esters, lecithin, paraffins

Definitions

  • This invention pertains to the use of a new type of natural triglyceride in food compositions to yield a product lower in calories.
  • These triglycerides strategically position saturated, long chain fatty acids and a short chain acid to achieve the desired balance of caloric availability and functional properties.
  • Fats make up 40% to 45% of the calories in the average American diet with triglycerides constituting about 90% of the total edible fats consumed. Fats provide approximately nine calories per gram compared to approximately four calories per gram for proteins and carbohydrates. Thus, major research efforts have been conducted toward the reduction of caloric intake for health or medical reasons without sacrificing the functional and organoleptic properties of fat.
  • a second strategy for developing reduced calorie replacement fats has been to synthesize nonabsorbable polymeric materials structurally unlike triglycerides, but having physical properties similar to edible fats.
  • Mineral oil was disclosed as early as 1894 (U.S. Patent No. 519,980, Winter) and, more recently, polydextrose (U.S. Patent No. 4,631,196, Zeller); polyglucose and polymaltose (U.S. Patent No. 3,876,794, Rennhard); polysiloxane (Eur. Patent Appl. No. 205,273, Frye); jojoba wax (W. Ger. Pat. No. 3,529,564, Anika); and polyethylene polymers (E. Ger. Patent No. 207,070, Ricoh, et al. ) have been suggested.
  • a third strategy for developing reduced calorie replacement fats combines the first two. Rather than restructure triglyceride molecules or find a substitute which is structurally dissimilar, this approach uses various polyol esters, compounds which have numbers of fatty acid groups in excess of the three in conventional triglyceride fats, as nonabsorbable fat replacements. For example, fully esterified sugar alcohols (Lapworth and Pearson, and Halliburton, et al., 13 J. Biol. Chem. 296 and 301 (1919)); esterified pentaerythritol, a tetrahydric neopentyl sugar alcohol which can be formed from pentaerythrose (U.S. Patent No.
  • Nondigestible or nonabsorbable triglyceride analogs, polyol esters, and polymeric materials have proven disappointing as fat replacements because, when tested in feeding trials, they caused gastrointestinal side effects, in some cases so extreme that frank anal leakage was observed (Hamm, 49 J. Food Sci. 419 (1984), Haumann, 63 J. Amer. Oil Chem. Soc. 278 (1986), and LaBarge, 42 Food Tech. 84 (1988)).
  • various hardened fats notably hydrogenated palm oils and synthetic cocoa butters, have been employed as anti-anal leakage agents to be used with sucrose polyesters (U.S. Patent Nos.
  • Sucrose polyesters also interfere with cholesterol metabolism and vitamin A and vitamin E absorption (Aust, et al., 25 Ann. Nutr. Metab. 255 (1981); Glueck, et al., 32 Amer. J. Clin. Nutr. 1636 (1979); and Sletten, et al. 7 Acta Vitaminal Enzymol. 49 (1985)). Polyesters stimulate the excretion of steroids in the feces (Glueck, at al., 33 Amer. J. Clin. Nutr. 2177 (1980)) and interfere with the metabolism of lipophlHc toxins (Richter, et al., 40 Chem. Biol. Interact. 335 (1982)).
  • An object of the present invention is to provide a new class of reduced calorie, all natural triglycerides and food compositions containing these products. Another object of this invention is to provide a fat composition that is substantially reduced in calories when compared to conventional fat compositions. A further object of this invention is to provide a fat which is at least partially nondigestible, thus yielding substantially fewer calories than conventional fat. A further object of this invention is to provide a reduced calorie fat having excellent organoleptic properties so that it can be used in a wide variety of foods. A further object of this invention is to provide a reduced calorie fat having excellent functional properties, i.e. melting, crystallization, and flavor transfer, so that it can be used in a wide variety of foods.
  • the short chain acid may be either saturated or unsaturated, either straight or branched.
  • the term natural means having the general characteristic structure of naturally occurring triglycerides, e.g. formed by the acid esterification of glycerol.
  • the term long chain means that the fatty acid contains at least about sixteen carbons.
  • the term short chain means that the acid contains no more than abou t ten carbons.
  • the new class of triglycerides are represented by the following formula: where, R and R" are long chain, saturated fatty acid residues containing between 16 and 40 carbons; and R' is a short chain acid residue containing between 2 and 10 carbons.
  • Reduced calorie fats can contain fatty materials in addition to the triglycerides of this invention which have a short-chain acid at the 2- position and saturated, long chain fatty acids at the 1- and 3- positions.
  • the triglycerides may be a pure composition consisting of only one triglyceride or a mixture of triglycerides. Where other fats are employed with these novel triglycerides, they should be of a type and in amounts compatible with the objects of this invention, primarily to reduce calories. Desirably, reduced calorie fats and edible foods of this invention will have predominant amounts of the novel triglycerides and, most usually, would contain at least 35%, and as much as 80% or higher of these triglycerides by weight.
  • the short chain acid should contain no more than about A carbons, preferably between 2 and 6 carbons, and more preferably between 2 and 4 carbons.
  • This short chain may be either saturated or unsaturated, straight or branched.
  • suitable short chain acids are acetic, propionic, n-butyric, iso-butyric, caproic, caprylic, pelargonic, capric, glycolic, lactic, hydracrylic, hydroxybutyric, propenoic, butenoic, pentenoic, hexenoic, heptenoic, octenoic, nonenoic, decenoic, and the like.
  • This short chain acid will be selected primarily for the calories it delivers and its effect on melting characteristics. In some circumstances, its effects on other properties will also be of importance.
  • the long chain fatty acids should be fully saturated with carbon chains containing between about 16 and about 40 carbons, preferably between 16 and 24 carbons, and more preferably between 16 and 20 carbons.
  • the long chain fatty acid at the 1- position may be either the same or different than that at the 3- position.
  • the long chain fatty acids which can be employed are palmitic, stearic, arachidic, behenic, lignoceric, cerotic, montanic, and melissic, as well as other less frequently occurring fatty acids.
  • the triglycerides can be structured so as to obtain the desired functional characteristics, such as melting point, for a variety of different food compositions.
  • esterifying with palmitic acid at the 1- and 3- positions would likely give a triglyceride with a lower melting point than if esterifying with behenic acid, and would thus be more suitable for incorporation into a butterscotch flavored chip.
  • esterifying with propionic acid at the 2- position of a dipalmitin a potentially monomorphic triglyceride is formed which has a higher degree of thermostability, a sharp melting point, and crystalline unity. This triglyceride would thus be appropriate in a food composition in which fat bloom is problematic, such as chocolate or the like coating.
  • fatty acids derived by the hydrolysis of natural fats can also be employed, such as those obtained from soybean, sunflower, peanut, safflower, olive, sesame, rice bran, canola, babassu, coconut, palm kernel, palm, rapeseed, cottonseed, corn, marine oil, or butter oil, or plant waxes such as jojoba.
  • Specific fractions of these processed or unprocessed oils or waxes can also be employed to provide fatty acid residues with aliphatic groups which impart specific, desired properties in the fat. For example, low molecular weight fatty acids derived from butter oil are desirable for the dairy flavor and aroma they impart upon partial hydrolysis.
  • hydrogenated fatty acids can be fractionated to provide fatty acids for triglycerides which melt within a desirable temperature range, e.g., just below body temperature. These characteristics can also be obtained by combinations of the triglycerides of this invention with those naturally present or used in food compositions.
  • the new class of triglycerides are represented by the following formula:
  • R and R" are long chain, saturated fatty acid residues containing between 16 and 40 carbons, preferably between 16 and 24 carbons, and more preferably between 16 and 20 carbons;
  • R' is a short chain acid residue containing between
  • triglycerides of this invention can be synthesized by tecnniques such as the direct or transesteriflcation of a selected 1,3-diglyceride (secondary alcohol).
  • tecnniques such as the direct or transesteriflcation of a selected 1,3-diglyceride (secondary alcohol).
  • the synthesis of several specific tailored triglycerides have been published: glyceryl valproates have been synthesized for use as anti-convulsants (U.S. Patent No. 4,701,469, Marriott, et al.); tailored triglycerides with a polyunsaturated, long chain fatty acid at the 2- position and a saturated fatty acid between C 4 and C 18 at the 1- and 3- positions have been synthesized for use as therapeutic compositions (U.S. Patent Nos.
  • the direct esteri fication reaction can be performed by reacting the 2-hydroxyl 1,3-diglyceride with the appropriate fatty acid, acid chloride, or acid anhydride.
  • pyridine or another type of base can be used to neutralize the hydrochloric acid by-product.
  • the direct esterification of the 1,3-diglyceride with the appropriate acid anhydride was found to be a preferred method for the preparation of the triglyceride esters of this invention.
  • fatty add moieties will affect the biological as well as the physical properties of the composition. Where these fatty acid moieties are metabolized, the caloric value of the compound will increase.
  • Preferred compounds are partially digestible and deliver 0.5 to 8.5 kcal/gram, preferably 0.5 to 6.0 kcal/gram, and more narrowly 1.0 to 5.0 kcal/gram upon being metabolized.
  • the triglycerides of this invention may be incorporated alone or in combination with another fat and/or fat substitute into any food composition or used in conjunction with any edible material.
  • edible material is broad and includes anything edible whether or not intended for nutrition, i.e., it can be an additive such as an antioxidant for fats or oils, an anti-spatter agent, an emulsifier, a texture modifier such as a plasticizer for chewing gum, a component for cosmetics, or other functional ingredient such as a carrier or diluent for use in flavorings, pharmaceuticals, and the like.
  • edible materials which can contain the fat of this invention in full or partial replacement of the currently used fat are: frozen deserts, i.e., sherbert, ice cream, ices, or milkshakes; puddings and pie fillings; margarine and margarine blends; flavored bread and biscuit spreads; mayonnaise; salad dressings; filled dairy products such as filled cream or milk; dairy or non-dairy cheese spreads; peanut butter spreads; coffee lighteners, liquid and dried; flavored dips; frying oils and fats; spray or topical oil; reformed and comminuted meats; meat substitutes and extenders; whipped toppings; compound coatings; frostings; confectionery coatings and fillings; cocoa butter replacements or blends; candy, especially fatty candies such as those containing peanut butter or chocolate; chewing gum; bakery products, i.e., cakes, breads, rolls, pastries, cookies, biscuits, and savory crackers; mixes or ingredient premixes for any of these; nuts, including peanuts;
  • the reduced calorie triglyceride fat, 2-acetyl-1,3-distearin is prepared in this example.
  • a reduced calorie sweet chocolate flavored comestible may be prepared by combining:
  • Sugar cookies may be prepared by blending:
  • Margarine may be prepared by combining the ingredients for the following two phases:
  • Beta Carotene 0.1 The phases are emulsified in an oil:aqueous phase ratio of 80:20, and passed through a cool scraped surface heat exchanger in the usual process.
  • Flavor Bits for incorporation into baked goods may be prepared by combining the following ingredients:
  • Dye 1 The first three ingredients are heated to 290oF. and the heat removed. Margarine is mixed in, and the mixture allowed to cool to 160-170oF. before adding the remaining ingredients. (Almost any flavoring material may be used as flavor, for example, butterscotch or peanut or other nut.) The mixture is then poured into a cold aluminum pan and frozen in dry ice. The frozen mixture is then cracked and milled into bits.
  • Butterscotch Cookies may be prepared by blending:
  • Example 6 Butterscotch bits 19.0 are mixed in until just blended prior to depositing and baking by the usual process.
  • vanilla Wafers To prepare vanilla wafers, blend
  • the dough so formed may be rolled, wire cut to 1/4 inch thickness, and baked by the usual process to give a vanilla wafer cookie.
  • Chocolate Chip Cookies may be prepared using the butterscotch cookie recipe of example 7. but substituting Ingredient Parts
  • Vanilla ice cream may be prepared by mixing:
  • vanilla Extract 0.8 and mix 1 minute. Cool and freeze while rotating to desired overrun.
  • the mixture is fermented and pressed to a final composition of approximately 37.0% moisture, 63.0%total solids, and 32.0% fat.
  • Butter Cream Icing may be prepared by blending:
  • Water 28 is sheeted, stamped, and baked to produce a cracker product
  • the sheeted and stamped cracker dough of example 15 may be sprayed with liquid 2-butyryl 1,3-dipalmitin after baking.
  • Mayonnaise can be prepared from the following formulation: Ingredient Parts
  • the egg yolk is first mixed with the other dry ingredients and a small amount of the water and vinegar in a container.
  • Liquid 2-butyryl 1,3-dipalmitin and corn oil are slowly poured into the container, while subjecting the container contents to mixing, to form an emulsion. While continuing to agitate the emulsion, the remaining water and vinegar is added.
  • Example 18 Liquid 2-butyryl 1,3-dipalmitin and corn oil are slowly poured into the container, while subjecting the container contents to mixing, to form an emulsion. While continuing to agitate the emulsion, the remaining water and vinegar is added.
  • Pudding can be prepared from the following formulation:
  • the ingredients can be blended together to form a pudding.
  • Pet Food. Dry, expanded animal food kibs may be prepared from the following ingredients:
  • Vitamins and Minerals 0.1 The ingredients are mixed together and water added to raise the water content to 27%, before extrusion, pelleting, and frying in the usual manner.

Abstract

Des triglycérides sont estérifiés dans les positions 1 et 3 avec des acides gras saturés à chaîne longue tels que l'acide stéarique et en position 2 avec un acide à chaîne courte tel que l'acide acétique. Ces triglycérides produisent moins de calories que les triglycérides généralement présents dans les aliments. Des compositions alimentaires à plus faible teneur en calories que les compositions d'origine peuvent ainsi être produites en remplaçant une partie ou la totalité de la matière grasse avec ce type de triglycéride.
PCT/US1990/005306 1989-09-20 1990-09-18 Triglycerides a teneur en calories reduite dans des aliments WO1991003944A1 (fr)

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US410,161 1989-09-20

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EP (1) EP0445278A4 (fr)
JP (1) JPH04501812A (fr)
AU (1) AU6509090A (fr)
CA (1) CA2042057A1 (fr)
WO (1) WO1991003944A1 (fr)

Cited By (13)

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Publication number Priority date Publication date Assignee Title
US5142071A (en) * 1989-12-19 1992-08-25 The Procter & Gamble Company Selective esterification of long chain fatty acid monoglycerides with medium chain fatty acids
DE4116004A1 (de) * 1991-05-16 1992-11-19 Fresenius Ag Naehrstoffzubereitung
EP0625874A1 (fr) * 1992-12-03 1994-11-30 Nabisco, Inc. Sable a effet rafraichissant perceptible
US5407695A (en) * 1989-09-20 1995-04-18 Nabisco, Inc. Low-palmitic, reduced-trans margarines and shortenings
EP0652714A1 (fr) * 1992-08-03 1995-05-17 Nabisco, Inc. Procede de preparation de centres mous pour produits alimentaires
EP0665718A1 (fr) * 1992-10-21 1995-08-09 Nabisco, Inc. Creme de garniture a prise rapide pour biscuits fourres
EP0680262A4 (fr) * 1993-01-22 1995-09-13 Nabisco Inc Huiles comestibles a pulveriser.
EP0671888A1 (fr) * 1992-12-02 1995-09-20 Nabisco, Inc. Fonds croustillants pour tartes restant fermes apres leur remplissage
EP0675688A1 (fr) * 1992-12-23 1995-10-11 Nabisco, Inc. Procede de modulation de la geometrie de biscuits
US5849353A (en) * 1995-09-01 1998-12-15 Hershey Foods Corporation Process to prevent bloom in chocolate products that contain fat substitutes
US7041840B2 (en) 2002-12-18 2006-05-09 Alberta Research Council Inc. Antioxidant triacylglycerols and lipid compositions
US8206772B2 (en) 2007-11-08 2012-06-26 Kraft Foods Global Brands Llc Structured lipid compositions and methods of formulation thereof
US8486478B2 (en) 2007-11-08 2013-07-16 International Great Brands LLC Structured lipid compositions

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US6835408B2 (en) 1998-11-13 2004-12-28 The Nisshin Oillio Group, Ltd. Oil or fat composition

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JPS649042A (en) * 1987-07-01 1989-01-12 Kanto Jidosha Kogyo Kk Thigh supporting device for seat cushion
JPH02158695A (ja) * 1988-12-10 1990-06-19 Fuji Oil Co Ltd 食餌用油脂及びこれを含有する食品
EP0322027B1 (fr) * 1987-12-15 1993-05-19 The Procter & Gamble Company Matières grasses ayant une teneur réduite en calories à partir de triglycérides contenant des acides gras à chaîne moyenne et longue

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CA2051640A1 (fr) * 1989-04-07 1990-10-08 Bruce R. Bistrian Triglycerides a chaine courte

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JPS649042A (en) * 1987-07-01 1989-01-12 Kanto Jidosha Kogyo Kk Thigh supporting device for seat cushion
EP0322027B1 (fr) * 1987-12-15 1993-05-19 The Procter & Gamble Company Matières grasses ayant une teneur réduite en calories à partir de triglycérides contenant des acides gras à chaîne moyenne et longue
JPH02158695A (ja) * 1988-12-10 1990-06-19 Fuji Oil Co Ltd 食餌用油脂及びこれを含有する食品

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Journal of Biological Chemistry, Vol. 258, 1983, WANG et al., "Studies on the Substrate Specificity of Purified Human Milk Bile Salt-Activated Lipase". See page 9197, col. 2, lines 16-19. *
Journal of Dairy Science, Vol. 47, 1964, JENSEN et al.., "Intermolecular Specificity of Pancreatic Lipase and the Structural Analysis of Milk Triglycerides". See the Abstract. *
Journal of Nutrition, Vol. 109, 1979, MATTSON et al., "The Absorbability by Rats of Various Triglycerides os Stearic and Oleic Acid and the Effect of Dietary Calcium and Magnesium". See the Abstract. *
Journal of the American Oil Chemists Society, Vol. 55, 1978, GRAY et al., "Polymorphism of Saturated Triglycerides: II. 1,3-Dipalmito Triglycerides". See Abstract and page 604, col. 1, lines 1-26. *
Journal of the American Oil chemists Society, Vol. 55, 1978, LOVEGREN et al., "Polymorphism of Saturated Triglycerids: I. 1,3-Distearo Triglycerides". See the Abstract and page 314, col. 2, lines 24-64. *
See also references of EP0445278A4 *

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5407695A (en) * 1989-09-20 1995-04-18 Nabisco, Inc. Low-palmitic, reduced-trans margarines and shortenings
US5142071A (en) * 1989-12-19 1992-08-25 The Procter & Gamble Company Selective esterification of long chain fatty acid monoglycerides with medium chain fatty acids
US5492713A (en) * 1991-05-16 1996-02-20 Sommermeyer; Klaus Nutriment preparation
DE4116004A1 (de) * 1991-05-16 1992-11-19 Fresenius Ag Naehrstoffzubereitung
WO1992020241A1 (fr) * 1991-05-16 1992-11-26 Fresenius Ag Preparation de substances nutritives
EP0652714A4 (fr) * 1992-08-03 1998-11-18 Nabisco Inc Procede de preparation de centres mous pour produits alimentaires.
EP0652714A1 (fr) * 1992-08-03 1995-05-17 Nabisco, Inc. Procede de preparation de centres mous pour produits alimentaires
EP0665718A4 (fr) * 1992-10-21 1999-04-28 Nabisco Inc Creme de garniture a prise rapide pour biscuits fourres.
EP0665718A1 (fr) * 1992-10-21 1995-08-09 Nabisco, Inc. Creme de garniture a prise rapide pour biscuits fourres
EP0671888A1 (fr) * 1992-12-02 1995-09-20 Nabisco, Inc. Fonds croustillants pour tartes restant fermes apres leur remplissage
EP0671888A4 (fr) * 1992-12-02 1997-02-26 Nabisco Inc Fonds croustillants pour tartes restant fermes apres leur remplissage.
EP0625874A1 (fr) * 1992-12-03 1994-11-30 Nabisco, Inc. Sable a effet rafraichissant perceptible
EP0625874A4 (en) * 1992-12-03 1997-02-26 Nabisco Inc Shortbread having a perceptible cooling sensation.
EP0675688A1 (fr) * 1992-12-23 1995-10-11 Nabisco, Inc. Procede de modulation de la geometrie de biscuits
EP0675688A4 (fr) * 1992-12-23 1997-02-26 Nabisco Inc Procede de modulation de la geometrie de biscuits.
EP0680262A1 (fr) * 1993-01-22 1995-11-08 Nabisco, Inc. Huiles comestibles a pulveriser
EP0680262A4 (fr) * 1993-01-22 1995-09-13 Nabisco Inc Huiles comestibles a pulveriser.
US5849353A (en) * 1995-09-01 1998-12-15 Hershey Foods Corporation Process to prevent bloom in chocolate products that contain fat substitutes
US7041840B2 (en) 2002-12-18 2006-05-09 Alberta Research Council Inc. Antioxidant triacylglycerols and lipid compositions
US8206772B2 (en) 2007-11-08 2012-06-26 Kraft Foods Global Brands Llc Structured lipid compositions and methods of formulation thereof
US8486478B2 (en) 2007-11-08 2013-07-16 International Great Brands LLC Structured lipid compositions
US8911813B2 (en) 2007-11-08 2014-12-16 Intercontinental Great Brands Llc Structured lipid compositions

Also Published As

Publication number Publication date
EP0445278A4 (en) 1992-03-11
CA2042057A1 (fr) 1991-03-21
AU6509090A (en) 1991-04-18
EP0445278A1 (fr) 1991-09-11
JPH04501812A (ja) 1992-04-02

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